Since the age of 17, im 31 now, I've never been to a hairdresser.
I used to be a metal/punk/hardcore kid and would get bored of a hairstyle very quickly so to save cash, I taught myself to cut/shave/dye my own hair and after a couple of dodgy efforts, soon became awesome at it.
Looking back, none of them embarrass me but just before that (around 16-17) I had a terrible hairstyle that I would love to have never happened.
Shaved back and sides, undercut-style, with the top down to my ears.....braided in a centre-parting. I'm white but looked a bit like some Nigerian footballer circa 1994. I also used to put beads at the bottom of each braid, and eventually tried turning them into proper dreadlocks...that's a disaster for another time and resulted in me always having short hair from then on.
Nowadays, I still do my own hair but being 31, stick to grade 2 back and sides, short on top, little bit of styling wax and no bleach as my already thinning hair would be done for!